First answer: Shitty trust fund management.
Second answer: A sociological cataloguing of the beasts might note that the lower upper class operates largely from diluted trust funds, private schools and clubs a tad threadbare at the seams, and parochial and localized haunts. Had Poppy not acquired the Presidency, W would surely be located here since rumor has it that Uncle Jonathan is not the ablest shepherds of the family fortune and W's apple didn't fall far from Uncle's tree.
Rephrase it: what are the relationships among the vertical and horizontal factions of the ruling class?